Heterocyclic Building Blocks-Naphthyridine

7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 3.1: 7-Bromo-[1,5]naphthyridin-2-ylamine [Show Image] In a sealed reactor, 500 mg (1.23 mmol, 1 eq) of 7-bromo-2-chloro-1,5-naphthyridine and 7 mL (41.6 mmol, 33 eq) of 20% aqueous ammonia solution were introduced in 7 mL of dioxane. The mixture was stirred at 160 C for 24 h. The mixture was allowed to reach rt and water was added. Aqueous layer was extracted with ethyl acetate. Organic layers were dried over Na2SO4, filtered and evaporated to dryness. The residue was purified by column chromatography using methylene chloride and then methylene chloride /ethanol : 98/2 as eluent. The solvent was evaporated to dryness to afford 220 mg of white powder with 80% yield. Yield: 220 mg (80 % of theory). m.p.: 168-169 C. 1H-NMR (DMSO-d6, 400 MHz): delta.= 8,57 (d, 1H); 8,05 (d, 1H); 7,96 (d, 1H); 6,04 (d, 1H); 6,98 (s, 2H) ppm. MS: m/z 225 (M+H+)., 1309774-03-5

1309774-03-5 is used more and more widely, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

Reference£º
Patent; Aeterna Zentaris GmbH; EP2332939; (2011); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

1,5-Naphthyridine, cas is 254-79-5, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 12; 220 221 222Part A: To a solution of compound 220 (1.0Og, 6.02 mmol) in carbon tetrachloride (60 ml_) was added dropwise, bromine (1.15 g, 7.20 mmol) as a carbon tetrachloride solution (6 mL). The resulting solution was refluxed for 1 hour. Pyridine (0.5 ml_, 6.0 mmol) as a carbon tetrachloride solution (10 mL) was added over a period of 1 hour to the refluxing reaction mixture. The reaction was stirred at reflux for 16 hours at which time LC-MS indicated that the reaction was complete. The reaction mixture was cooled to room temperature, resulting in the formation of a precipitate, which was filtered. The carbon tetrachloride filtrate was set aside. The collected brown solid was taken up in 10% NaOH (100 mL) and stirred at room temperature for 1 hour. This solution was extratcted with chloroform. The chloroform and carbon tetrachloride solutions were combined and concentrated in vacuum. Purification by column chromatography (Sitheta2, 20% EtOAc / DCM) afforded compound 221 as a white solid 0.17 g, (14%). 1H NMR (400 MHz, DMSO-d6) delta 9.07 (d, 1 H), 9.02 (dd, 1 H), 8.74 (m, 1 H), 8.45 (m, 1 H), 7.83 (dd, 1 H)., 254-79-5

With the rapid development of chemical substances, we look forward to future research findings about 1,5-Naphthyridine

Reference£º
Patent; SCHERING CORPORATION; WO2008/82487; (2008); A2;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,3-Bromo-1,5-naphthyridine,17965-71-8,Molecular formula: C8H5BrN2,mainly used in chemical industry, its synthesis route is as follows.,17965-71-8

3-bromonaphthyridine (44.5 g, 0.213 mol), absolute ethanol (357 mL),N,N-dimethylformamide (90 mL) was added, palladium chloride (2.65 g), triethylamine (32.28 g, 0.32 mol),The reaction liquid was spin-dried by reacting carbon monoxide at a pressure of 0.8 MPa at 75 C for 6 h.Use petroleum ether: ethyl acetate = 10:1 ~ 1:1 over the column,Methyl 1,5-naphthyridin-3carboxylate (34 g, white solid, yield 84%).

With the synthetic route has been constantly updated, we look forward to future research findings about 3-Bromo-1,5-naphthyridine,belong naphthyridine compound

Reference£º
Patent; Suzhou Kangrun Pharmaceutical Co., Ltd.; Jin Haowen; Xu Weiliang; Xu Weizheng; (8 pag.)CN108658977; (2018); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to naphthyridine compound, name is 1,8-Naphthyridine-2-carboxylic acid, and cas is 215523-34-5, its synthesis route is as follows.,215523-34-5

To a solution OF 4- [ (4-BROMOPHENYL) (ethoxyimino) methyl]-1-(4-methyl-4- piperidinyl) piperidine (50 mg, 0.12 MMOL), 1, 8-naphthyridine-2-carboxylic acid (25 mg, 0.14 MMOL), and Et3N (44 mg, 0.43 MMOL) in DMF (3 mL, anhydrous) was added HATU (60 mg, 0.16 MMOL) at room temperature. After 16 h the reaction mixture was poured into ice water, and the solid was collected by filtration. The solid was dissolved in CH2CI2 and dried over NA2S04. Concentration in vacuo, and purification by preparative TLC (CH2CI2-MEOH, 9: 1) afforded the title compound as a light brown powder. MS: 564 (M+).

With the complex challenges of chemical substances, we look forward to future research findings about 215523-34-5,belong naphthyridine compound

Reference£º
Patent; SCHERING AKTIENGESELLSCHAFT; WO2004/113323; (2004); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

It is a common heterocyclic compound, the naphthyridine compound, 7-Bromo-2-chloro-1,5-naphthyridine, cas is 1309774-03-5 its synthesis route is as follows.,1309774-03-5

0384-2 A mixture of 7-bromo-2-chloro-1,5-naphthyridine (32 mg), bis(pinacolato)diboron (50 mg), (1,1′-bis(diphenylphosphino)ferrocene)palladium(II) dichloride (11 mg), potassium acetate (26 mg), and 1,4-dioxane (1 mL) was stirred at 80 C. for 2 hours in a nitrogen atmosphere. The reaction mixture was cooled to room temperature, and 4-(3-(4-iodo-3-methyl-1H-pyrazol-1-yl)propyl)morpholine (44 mg), sodium carbonate (28 mg), bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium(II) (9 mg), and water (0.1 mL) were added thereto, followed by stirring at 80 C. for 2 hours. The reaction mixture was cooled to room temperature, the insolubles were filtered off using celite, and the solvent was distilled off under reduced pressure. The obtained residue was purified by silica gel column chromatography (methanol-ethyl acetate, NH silica), thereby obtaining 4-(3-(4-(6-chloro-1,5-naphthyridin-3-yl)-3-methyl-1H-pyrazol-1-yl)propyl)morpholine (10 mg). MS m/z (M+H): 372.

With the complex challenges of chemical substances, we look forward to future research findings about 7-Bromo-2-chloro-1,5-naphthyridine

Reference£º
Patent; FUJIFILM Corporation; FURUYAMA, Hidetomo; KURIHARA, Hideki; TERAO, Takahiro; NAKAGAWA, Daisuke; TANABE, Shintaro; KATO, Takayuki; YAMAMOTO, Masahiko; SEKINE, Shinichiro; MASHIKO, Tomoyuki; INUKI, Shinsuke; UEDA, Satoshi; US2015/322063; (2015); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate, cas is 100491-29-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

Example 7 7-Chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic acid. A mixture of tetrahydrofuran (450 cm3), water (50 cm3), methanesulfonic acid (127 cm3) and ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylate (United Kingdom Patent Publication No. GB 2,191,776) was heated at reflux for 1 hour, and then cooled to 25C. The resulting crystals were isolated, washed with tetrahydrofuran, and dried under vacuum to afford 41.3g (89%) of the above-titled compound: m.p. = 250C; (Found: C, 50.4; H, 1.7; Cl, 9.9; F, 16.0; N, 8.0. C15H6CIF3N2O3requires C, 50.8; H, 1.7; Cl, 10.0; F, 16.1; N, 7.9%); 1H NMR (300 MHz, d6-DMSO) delta 13.9 (s, 1H), 9.09 (s, 1H), 8.77 (d, J= 7.5 Hz, 1H), 7.86 (td, J= 5.9 and 8.8 Hz, 1H), 7.66 (ddd, J= 2.7, 9.0 and 11.8 Hz, 1H), 7.39 (tm, J= 8.6 Hz, 1H), 7.39 (tm, J= 8.6 Hz, 1H); numax(DRIFTS) cm-13130, 3060, 2947, 2885, 2821, 2723, 2637, 2594, 1734, 1641, 1623, 1579, 1544,1516., 100491-29-0

With the rapid development of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate

Reference£º
Patent; Pfizer Products Inc.; EP976749; (2000); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

2-Methyl[1,8]-Naphthyridine, cas is 1569-16-0, it is a common heterocyclic compound, the naphthyridine compound, its synthesis route is as follows.

[00228] A solution of 2-methyl-l,8-naphthyridine (5.0 g, 34.7 mmol) in tetrahydrofuran (60 mL) was stirred at -78 ¡ãC and MeLi (2 M solution in tetrahydrofuran, 52 mL, 104 mmol) was added dropwise. The mixture was warmed to room temperature and stirred for 16 h. The reaction mixture was diluted with water (50niL), extracted with ether (3 x 50 rnL) and the combined the organic layers were dried over anhydrous sodium sulfate, concentrated under reduced pressure, and purified by flash chromatography eluting with ethyl acetate:petrol ether (1 : 10) to give the title compound as a white solid (4.55 g, 82percent). MS (ESI): m/z 161 [M + H]+., 1569-16-0

1569-16-0 is used more and more widely, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine

Reference£º
Patent; SUNOVION PHARMACEUTICALS INC.; CAMPBELL, John Emmerson; JONES, Philip; WO2014/85284; (2014); A1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belongs to quinuclidine compound,Quinuclidine-4-carboxylic acid hydrochloride,40117-63-3,Molecular formula: C8H14ClNO68,mainly used in chemical industry, its synthesis route is as follows.,100491-29-0

General procedure: Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate (1) / carboxylic acid (2) (0.001 mol) and appropriate substituted benzazol-2-thiol derivative (0.001 mol) or N,N- dimethyl-(3-piperazin-1-yl)propan-1-amine (0.001 mol) and K2CO3 were dissolved in acetone (30 mL). The solution was refluxed at 40 C for 12 h. Reaction mixture was cooled down and adjusted to pH=7 by AcOH. Acetone was evaporated, the residue was washed with water, filtered, dried and recrystallized from EtOH.

With the complex challenges of chemical substances, we look forward to future research findings about Ethyl 7-chloro-1-(2,4-difluorophenyl)-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylate,belong naphthyridine compound

Reference£º
Article; Gencer, Huelya Karaca; Levent, Serkan; Acar Cevik, Ulviye; Oezkay, Yusuf; Ilg?n, Sinem; Bioorganic and Medicinal Chemistry Letters; vol. 27; 5; (2017); p. 1162 – 1168;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,2-Methyl[1,8]-Naphthyridine,1569-16-0,Molecular formula: C9H8N2,mainly used in chemical industry, its synthesis route is as follows.,1569-16-0

adding 0.3 mmol of 2-methyl-1,8-naphthyridine, 0.75 mmol of elemental iodine, and 2 mL of dimethyl sulfoxide to a 15 mL pressure-resistant tube.The reaction was stirred magnetically at 110 C for 4 hours. After the reaction was cooled, 0.36 mmol of p-toluenesulfonylhydrazide and 0.9 mmol of potassium phosphate trihydrate were added, and magnetic stirring was carried out at 110 C for 6 hours. After the reaction was completed, the reaction solution was completed. Extraction, organic layer washing, drying, distillation under reduced pressure to obtain a crude product, crude product with petroleum ether / ethyl acetate = 1.5:1 ~ 2:1 (V / V) as the eluent for column separation and purification The desired product, the product is a yellow solid with a yield of 65%.

With the synthetic route has been constantly updated, we look forward to future research findings about 2-Methyl[1,8]-Naphthyridine,belong naphthyridine compound

Reference£º
Patent; Yantai University; Zhu Yanping; Lv Xucheng; Sun Jina; He Hangli; Sun Yuanyuan; Weng Weizhao; Wang Ru; Lv Lijuan; Huang Qiang; (17 pag.)CN110105355; (2019); A;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem

As a common heterocyclic compound, it belong naphthyridine compound,7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,100361-18-0,Molecular formula: C12H8ClFN2O3,mainly used in chemical industry, its synthesis route is as follows.,100361-18-0

Triethylamine (34ml) was added to 7-chloro-1-cyclopropyl-6-fluoro-4-oxo-1,4-dihydro-1,8-naphthyridine-3-carboxylic acid (20.17g) in a mixture of acetonitrile (100ml) and water (100ml) at 15-20C and the mixture stirred for 30 min. 4-Aminomethyl-3-methoxyiminopyrrolidinium dihydrochloride (18.9g) was added, followed by water (5ml), and the mixture stirred at 20-25C for 23? hours. The resulting product was filtered and the cake washed with ice-cold 1:2 acetonitrile:water (100ml) followed by acetonitrile (100ml), air dried, then dried under vacuum, at ambient temperature, to give the title compound as a fawn solid (26g). (94% as is, 78.8% on assay). Characterising data were consistent with a standard sample of the title compound.

With the synthetic route has been constantly updated, we look forward to future research findings about 7-Chloro-1-cyclopropyl-6-fluoro-1,4-dihydro-4-oxo-1,8-naphthyridine-3-carboxylic Acid,belong naphthyridine compound

Reference£º
Patent; LG Life Sciences, Ltd.; EP1214321; (2004); B1;,
1,8-Naphthyridine – Wikipedia
1,8-Naphthyridine | C8H6N2 – PubChem